1,2-Dichloroethane → N-(4-(Cyclopropylamino)-3,4-dioxo-1-phenylbutan-2-yl)-2-(2-phenylthiazol-4-yl)nicotinamide

HRID 1400234Notes

Reaction equation

HRID 1400234 reaction equation
C(Cl)CCl.ClC(Cl)C(O)=O.[CH:11]1([NH:14][C:15](=[O:46])[CH:16]([OH:45])[CH:17]([NH:25][C:26](=[O:44])[C:27]2[CH:32]=[CH:31][CH:30]=[N:29][C:28]=2[C:33]2[N:34]=[C:35]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[S:36][CH:37]=2)[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:13][CH2:12]1.C([O-])(O)=O.[Na+]>CS(C)=O>[CH:11]1([NH:14][C:15](=[O:46])[C:16](=[O:45])[CH:17]([NH:25][C:26](=[O:44])[C:27]2[CH:32]=[CH:31][CH:30]=[N:29][C:28]=2[C:33]2[N:34]=[C:35]([C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)[S:36][CH:37]=2)[CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:12][CH2:13]1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 6597Dichloroacetic AcidHCID 516892Sodium BicarbonateHCID 67539859N-(4-(Cyclopropylamino)-3-hydroxy-4-oxo-1-phenylbutan-2-yl)-2-(2-phenylthiazol-4-yl)nicotinamide

Product 1

HCID 46870677N-(4-(Cyclopropylamino)-3,4-dioxo-1-phenylbutan-2-yl)-2-(2-phenylthiazol-4-yl)nicotinamideYield 89.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

EDC (700 mg, 3.65 mmol) and 2,2-dichloroacetic acid (12411, 1.46 mmol) were added to a solution of N-(4-(cyclopropylamino)-3-hydroxy-4-oxo-1-phenylbutan-2-yl)-2-(2-phenylthiazol-4-yl)nicotinamide (217 mg, 0.435 mmol) in dimethyl sulfoxide (DMSO) (4 ml), and the reaction mixture stirred for 10 min at room temperature. For work up the reaction mixture was mixed with 80 ml of sat. NaHCO3-solution for 10 minutes. The resulting solid was filtered off with suction, washed with water and dried in vacuo to give 193 mg of the title product as white amorphous solid;

Workup

  1. filtrationThe resulting solid was filtered off with suction
  2. washwashed with water
  3. customdried in vacuo

Sources & evidence

ORD record
ord-0e6c121b90394dbebbad3edba022ca83
Source dataset
uspto-grants-2014_12
Patent number
US08906941B2

Reaction notes

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